GB854956A - Aromatic sulphonyl amino compounds containing trifluoromethyl radicals - Google Patents

Aromatic sulphonyl amino compounds containing trifluoromethyl radicals

Info

Publication number
GB854956A
GB854956A GB3671557A GB3671557A GB854956A GB 854956 A GB854956 A GB 854956A GB 3671557 A GB3671557 A GB 3671557A GB 3671557 A GB3671557 A GB 3671557A GB 854956 A GB854956 A GB 854956A
Authority
GB
United Kingdom
Prior art keywords
trifluoromethyl
chloromethane
chloro
compounds
sulphochloride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3671557A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DEF21888A external-priority patent/DE1058049B/en
Priority claimed from DEF22658A external-priority patent/DE1062238B/en
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB854956A publication Critical patent/GB854956A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • C09B43/1247—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters with formation of NHSO2R or NHSO3H radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises aromatic sulphonylamino compounds containing the trifluoromethyl radical-CF3 and having the general formulae: <FORM:0854956/IV(b)/1> wherein X stands for hydrogen, chlorine or the trifluoromethyl radical-CF3, at least one X being CF3, R stands for a chloroalkyl-, chlorocycloalkyl-, chloroaryl-, or chloroaralkyl radical, and Y stands for a diphenyl linkage or for O, S, SO, SO2, or CH2. The compounds are obtained by reacting monoof bi-nuclear aromatic amines, substituted in a nucleus with CF3, with the appropriate chloro-sulphochlorides followed, if desired, by direct chlorination. The compounds are effective protective agents against textile pests, fungi, and bacteria (see Group VIII). In Example 1, a pyridine solution of 41-chloro-4-trifluoromethyl-2-amino-1,11-diphenyl ether is treated at 0 DEG C. with chloromethane-sulphochloride. After standing for 12 hours at room temperature, the solution is poured into water whereby a precipitate comprising 41chloro-4-trifluoromethyl-2-chloromethane-sulphonylamino-1, 11-diphenyl ether is obtained. In Example 2, the product of Example 1 is dissolved in glacial acetic acid, and subjected to direct chlorination using ferric chloride as catalyst, whereby another chlorine atom is introduced into the molecule. Example 5 describes the condensation of 2, 4, 5-trichlorophenol with 3-nitro-4-chloro-benzotrifluoride, the reduction of the nitro condensation product to the corresponding amine, and the reaction of the latter with chloromethane-sulphochloride to yield 4-trifluoromethyl-2-chloromethane-sulphonamino-21, 41, 51trichloro-1, 11-diphenyl ether. When 2, 4, 5-trichlorothiophenol is employed in place of the trichlorophenol there is obtained 4-trifluoromethyl-2-chloromethane-sulphonylamino-21, 41, 51-trichloro-1, 11-diphenylsulphide, and this may be oxidized to the corresponding sulphoxide or sulphone. In Example 9, chloromethane sulphochloride is reacted with 2-fluoro-5-trifluoromethyl aniline to yield 2-fluoro-5-trifluoromethyl-1-chloromethane sulphonylaminobenzene. This example also refers to the preparation of 2-chloro-5-trifluoromethyl-41-chlorophenylsulphonyl -aminobenzene; also the corresponding 31, 41-dichloro-and 21, 41, 51 trichloro-compounds. Specifications 702,602, 709,455 and 738,758 are referred to.
GB3671557A 1956-12-08 1957-11-25 Aromatic sulphonyl amino compounds containing trifluoromethyl radicals Expired GB854956A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEF21888A DE1058049B (en) 1956-12-08 1956-12-08 Process for the production of protective agents against textile pests, mold and bacterial attack
DEF22658A DE1062238B (en) 1957-03-23 1957-03-23 Process for the production of protective agents against textile pests, mold and bacterial attack
DEF0026477 1958-08-23

Publications (1)

Publication Number Publication Date
GB854956A true GB854956A (en) 1960-11-23

Family

ID=27210052

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3671557A Expired GB854956A (en) 1956-12-08 1957-11-25 Aromatic sulphonyl amino compounds containing trifluoromethyl radicals
GB2623459A Expired GB900111A (en) 1956-12-08 1959-07-30 Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicides

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2623459A Expired GB900111A (en) 1956-12-08 1959-07-30 Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicides

Country Status (4)

Country Link
CH (2) CH366038A (en)
DE (1) DE1418197A1 (en)
GB (2) GB854956A (en)
SE (1) SE303127B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3239564A (en) * 1960-12-02 1966-03-08 Reeder Earl 2 n-substituted amino halobenzo-phenones

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL301745A (en) * 1962-12-17
US3953492A (en) * 1975-03-27 1976-04-27 Merck & Co., Inc. Anthelmintic substituted sulfonamide derivatives
US3953493A (en) * 1975-03-27 1976-04-27 Merck & Co., Inc. Substituted sulfonamide derivatives as anthelmintic agents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3239564A (en) * 1960-12-02 1966-03-08 Reeder Earl 2 n-substituted amino halobenzo-phenones

Also Published As

Publication number Publication date
CH366038A (en) 1962-12-15
DE1418197A1 (en) 1968-10-17
GB900111A (en) 1962-07-04
CH388297A (en) 1965-02-28
SE303127B (en) 1968-08-19

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